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The Accounting Podcast

How Sam Leon Uses Claude Cowork to Prep Tax Returns 5x Faster

July 25 · 1 hr 7 min · Episode 497 · 65.1 MB
0:00-1:07:46

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Can one accountant really do tax prep five times faster with AI? Blake and David talk with Sam Leon, founder of The Millennial CPA, about how he uses Claude projects to turn client documents into tax workpapers, speed up review, and run a solo firm built around software. They also dig into where AI still falls short, why review remains the bottleneck, and what firms can realistically automate today.

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Chapters
  • (00:00) - Autonomous AI Reality Check
  • (00:11) - Show Welcome and Interview Tease
  • (00:55) - Sponsor Spotlight Digits
  • (02:34) - Trump IRS Deal Dismissed
  • (05:20) - California Billionaire Tax Fight
  • (07:35) - New York Pied a Terre Tax
  • (09:29) - Sponsor Spotlight Value Builder System
  • (11:18) - Xero CEO Pay and Stock Sale
  • (16:39) - Verification Tax and AI Jobs
  • (22:06) - Sponsor Spotlight OnPay
  • (23:21) - 1948 IBM Accounting Machine Lesson
  • (29:56) - Sponsor Spotlight Cloud Accountant Staffing
  • (31:07) - Meet Sam Leon Millennial CPA
  • (32:01) - Solo Firm Vision
  • (33:15) - From Big Firms to Millennial CPA
  • (35:42) - Why AI Agents Weren’t Ready
  • (37:19) - Automating Tax Prep Workflow
  • (40:33) - Smart Intake for Better Scoping
  • (43:06) - End to End Return Automation
  • (46:04) - AI Workpapers and Review
  • (49:38) - Claude Setup and Time Savings
  • (58:18) - Tech Spend and Pricing Strategy
  • (01:02:52) - Building TaxWeave Platform
  • (01:06:21) - Wrap Up and CPE Info
 


Show Notes

Judge Smacks Down Trump's IRS Settlement And Orders Sanctions

https://www.cnn.com/2026/07/13/politics/trump-irs-judge-ruling-settlement-sanctions

Instead of Uniting the Left, California's Billionaire Tax Measure Has Split Democratic Allies

https://www.cpapracticeadvisor.com/2026/07/08/instead-of-uniting-the-left-californias-billionaire-tax-measure-has-split-democratic-allies/186379/

NYC lawyers slam pied-a-terre tax as a half-baked money grab

https://www.audacy.com/1010wins/news/local/nyc-lawyers-slam-pied-a-terre-tax-as-a-half-baked-money-grab

A 1948 IBM computer with no memory at all, fed by punchcards, was still doing the accounting at a Texas filtration company as recently as 2020

https://scienceblog.com/t-1948-ibm-402-punchcards-sparkler-filters-accounting-2020/

Time saved by AI partially canceled out by time spent checking AI

https://www.accountingtoday.com/news/time-saved-by-ai-partially-cancelled-out-by-time-spent-checking-ai

Research Suggests Jobs May be Safer at Companies that Embrace AI

https://www.cpapracticeadvisor.com/2026/07/07/research-suggests-jobs-may-be-safer-at-companies-that-embrace-ai/186281/

AI Is No Longer Just a Tech Occupation Story: It's Spreading Across Job Titles in the US and Europe

https://www.hiringlab.org/2026/07/08/ai-is-no-longer-just-a-tech-occupation-story/

The 2026 Best Accounting Firms for Technology

https://www.accountingtoday.com/list/the-2026-best-accounting-firms-for-technology


Need CPE?

Get CPE for listening to podcasts with Earmark: https://earmarkcpe.com
Subscribe to the Earmark Podcast: https://podcast.earmarkcpe.com

Meet Our Guest, Sam Leon, CPA
LinkedIn: https://www.linkedin.com/in/samuelaaronleon/
Website: https://www.millennialcpa.tax/
Website: https://www.taxweave.ai/

Get in Touch

Thanks for listening and the great reviews! We appreciate you! Follow and tweet @BlakeTOliver and @DavidLeary. Find us on Facebook and Instagram. If you like what you hear, please do us a favor and write a review on Apple Podcasts or Podchaser. Call us and leave a voicemail; maybe we'll play it on the show. DIAL (202) 695-1040.


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